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Sidney Crosby gives the Penguins an intriguing ultimatum that likely leads to his departure in Pittsburgh


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Joshua Deeds
September 27, 2025  (8:34)
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Sidney Crosby
Photo credit: Charles LeClaire-Imagn Images

The trade rumors between the Penguins and Sidney Crosby persist, as Kyle Dubas is caught in the crossfire of Pat Brisson, who is set to make his job difficult after sending a clear ultimatum message to to the organization.

Trade speculation for Penguins Captain Sidney Crosby hasn't died down, as recent rumors linked him to the Montreal Canadiens.
Agent Pat Brisson sparked trade discussions throughout the NHL by taking a jab at Pittsburgh's current out-of-playoff state in the NHL, signalling Crosby will be heading somewhere with rich playoff success.
«Well, it's a reality,» Brisson told Pierre LeBrun. «First of all, he's been so consistent for 20 years. He had another great year last season. He just keeps going. The comparison is Tom Brady. We want Sidney to hopefully be in the playoffs every year. We want him to hopefully win another Cup or two. So each year the team that he's playing for fails to make the playoffs, it creates a lot of speculation. In reality, he's not getting any younger. We're here to support him. It's the beginning of the season here. Let's see how things are going. Hopefully they have a great season and the speculation will go away.»

While The Athletic's Josh Yohe believes the comment from Brisson was an ultimatum from GM Kyle Dubas of the Penguins.

Pat Brisson's Inflammatory Comments Regarding Sidney Crosby

«Pat Brisson said plenty of interesting things during his interview with Pierre LeBrun . I sense that Brisson probably would have handled some things differently if he could turn back time. But I also think Brisson will be very unhappy if the Penguins trade Rakell or Rust.

This could end up being a breaking point for the Penguins captain if he sees those two players' tenure at an end in Pittsburgh.
Of course, it'd be unrealistic to expect Dubas not to trade players like Rust, Rakell, or Erik Karlsson once the NHL season begins.
In fact, Yohe believes these rumors will gain traction:
«Those talks aren't going away. Dubas has made it clear that he's open for business.»

While ultimately, Evgeni Malkin and Sidney Crosby should finish out the year in Pittsburgh, even if Rust and Rakell don't.
«Crosby, in my opinion, isn't going anywhere, despite the recent comments from Brisson.

I'd also be surprised if Evgeni Malkin were to be dealt. It's possible. Malkin's comments last week were very interesting. He was pretty vulnerable in discussing the reality that he isn't quite sure what he'll do if another team comes calling.»

Kyle Dubas is in charge of rebuilding the Penguins without upsetting the team's best forward (this seems to be a monumental task at the moment).
This could be a challenging year for both Crosby and the general manager, who has begun his rebuild in hopes of returning to playoff contention.
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Sidney Crosby gives the Penguins an intriguing ultimatum that likely leads to his departure in Pittsburgh

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